File:Psilocybin,_Kekulé,_skeletal_formula_of_canonical_psilocybin.svg · Wikimedia Commons · See Wikimedia Commons
psilocybin
Sign in to saveAlso known as 4-PO-DMT, O-phosphoryl-4-hydroxy-N,N-dimethyltryptamine, 4-phosphoryloxy-N,N-dimethyltryptamine, psilocin phosphate ester, psilocybine, indocybin, 3-(2-(dimethylamino)ethyl)-1H-indol-4-ol dihydrogen phosphate ester, 3-(2-dimethylaminoethyl)indol-4-yl dihydrogen phosphate
Psilocybin, also known as '4-phosphoryloxy-N,N-dimethyltryptamine (4-PO-DMT'), is a naturally occurring tryptamine alkaloid and investigational drug found in more than 200 species of mushrooms, with hallucinogenic and serotonergic effects. Effects include euphoria, changes in perception, a distorted sense of time, and perceived spiritual experiences. It can also cause adverse reactions such as nausea and panic attacks.
OverviewAI-generated
Psilocybin is a chemical compound with the formula C₁₂H₁₇N₂O₄P. It has a mass of 284.093 and a boiling point of 523.44. The substance carries a charge of 0 and features 3 hydrogen bond donors and 5 hydrogen bond acceptors. Its xlogp value is -1.6, and its topological polar surface area is 85.8.
The compound is associated with 3,242 entries in PubMed literature. It is referenced by 2,765 other encyclopedia articles.
Synthesized by Vinony from 17 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
Key facts
- Drug.synonyms
- Psilocybine; Psilocibin; Psylocybin; Psilotsibin; Psilocin phosphate; Psilocin phosphate ester; O-Phosphorylpsilocin; O-Phosphoryl-4-hydroxy-N,N-dimethyltryptamine; 4-Phosphoryloxy-N,N-dimethyltryptamine; 4-PO-DMT; COMP360; COMP-360; CY-39; CY39; PSOP
- Drug.IUPAC_name
- [3-[2-(dimethylamino)ethyl]-1H-indol-4-yl] dihydrogen phosphate
- Drug.C
- 12
- Drug.H
- 17
- Drug.N
- 2
- Drug.O
- 4
- Drug.P
- 1
- Drug.SMILES
- CN(C)CCC1=CNC2=C1C(=CC=C2)OP(=O)(O)O
- Drug.StdInChI
- 1S/C12H17N2O4P/c1-14(2)7-6-9-8-13-10-4-3-5-11(12(9)10)18-19(15,16)17/h3-5,8,13H,6-7H2,1-2H3,(H2,15,16,17)
- Drug.StdInChIKey
- QVDSEJDULKLHCG-UHFFFAOYSA-N
- Drug.melting_point
- 220-228
- Drug.Watchedfields
- verified
- Drug.verifiedrevid
- 479504713
- Drug.INN
- Psilocybine
- Drug.USAN
- Psilocybin
- Drug.image
- Psilocybin, Kekulé, skeletal formula of canonical psilocybin.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 200px
via Wikipedia infobox
Chemical data
- Formula
- C12H17N2O4P
- Molecular weight
- 284.25 g/mol
- IUPAC name
- [3-[2-(dimethylamino)ethyl]-1H-indol-4-yl] dihydrogen phosphate
- SMILES
- CN(C)CCC1=CNC2=C1C(=CC=C2)OP(=O)(O)O
- InChIKey
- QVDSEJDULKLHCG-UHFFFAOYSA-N
- XLogP
- -1.6
- Polar surface area
- 85.8 Ų
- H-bond donors
- 3
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Research
3,242 papers- The Therapeutic Potential of Psilocybin.Molecules (Basel, Switzerland) · 2021
- Trial of Psilocybin versus Escitalopram for Depression.The New England journal of medicine · 2021
- Psilocybin: from ancient magic to modern medicine.The Journal of antibiotics · 2020
- Metabolism of psilocybin and psilocin: clinical and forensic toxicological relevance.Drug metabolism reviews · 2017
- Psilocybin for Trauma-Related Disorders.Current topics in behavioral neurosciences · 2022
via PubMed
~85 min read
Encyclopedic overview
49 sectionsContents
- Uses
- Medical
- Dosing
- Available forms
- Effects
- Psychological and perceptual effects
- Set and setting and moderating factors
- Theory of mind network and default mode network
- Group perceptions
- Cultural significance and "mystical" experiences
- Physical effects
- Onset and duration
- Contraindications
- Adverse effects
- Psychiatric adverse effects
- Tolerance and dependence
- Long-term effects
- Overdose
- Interactions
- Pharmacology
- Pharmacodynamics
- Pharmacokinetics
- Absorption
- Distribution
- Metabolism
- Elimination
- Miscellaneous
- Chemistry
- Physical properties
- Laboratory synthesis
- Analytical methods
- Structural analogues
- Natural occurrence
- Biosynthesis
- History
- Early
- Modern
- Society and culture
- Usage
- Legal status
- Advocacy for tolerance
- Research
- Psychiatric and other disorders
- Depression
- Obsessive–compulsive disorder
- See also
- Notes
- References
- External links
Psilocybin, also known as '4-phosphoryloxy-N,N-dimethyltryptamine (4-PO-DMT'), is a naturally occurring tryptamine alkaloid and investigational drug found in more than 200 species of mushrooms, with hallucinogenic and serotonergic effects. Effects include euphoria, changes in perception, a distorted sense of time, and perceived spiritual experiences. It can also cause adverse reactions such as nausea and panic attacks.
Psilocybin is a prodrug of psilocin. That is, the compound itself is biologically inactive but quickly converted by the body to psilocin. Psilocybin is transformed into psilocin by dephosphorylation mediated via phosphatase enzymes. Psilocin is chemically related to the neurotransmitter serotonin and acts as a non-selective agonist of the serotonin receptors. Activation of one serotonin receptor, the serotonin 5-HT2A receptor, is specifically responsible for the hallucinogenic effects of psilocin and other serotonergic psychedelics. Psilocybin is usually taken orally. By this route, its onset is about 20 to 50 minutes, peak effects occur in about 1 to 2 hours, and its duration is about 4 to 6 hours.
Excerpted from Wikipedia’s “psilocybin” article, available under the CC BY-SA 4.0 licence.